Blackface and Hollywood: From Al Jolson to Judy Garland to Dave Chappelle

"You can always bring it back in some ironic way," notes NYU cinema professor Ed Guerrero of the racist tradition at the center of a Virginia political scandal.

It was November 2004, and Dave Chappelle was filming the third season of Chappelle's Show for Comedy Central. After two seasons of mining edgy racial humor to great ratings success, Chappelle was eager to push the envelope to its breaking point.

He conceived of a series of sketches involving various racist "pixie" characters and cast himself as a "Black Pixie" — an ugly stereotype in blackface and a bellboy uniform that visits an airplane passenger (also played by Chappelle) and encourages him to order the fried chicken.

The sketch amused Chappelle in rehearsals, but when it screened for a live audience, Chappelle grew uneasy over the reaction of one man in the crowd. "When he laughed, it made me uncomfortable," Chappelle later recalled of the white man's chortling, which was just a little too loud and went on a little too long. "As a matter of fact," Chappelle said, "that was the last thing I shot before I told myself I gotta take fucking time-out after this. Because my head almost exploded."

What came next is now part of show-business lore: Chappelle walked away from the show that made him a megastar — and the $50 million payday that came with it. That anecdote speaks volumes about blackface — both about its complicated history in Hollywood, and the deep pain it can unleash, even upon someone as seemingly inured to such things as Chappelle.

Now, a decade-and-a-half later, the topic of blackface has reared its ugly head once again. While the collision of social media and Halloween always turns up a few instances every late October, the topic has now spilled over into the world of politics, after the surfacing of a disturbing photo on Virginia Gov. Ralph Northam's page in a 1984 medical school yearbook.

Northram says he is neither the figure in blackface nor the person beside it in Ku Klux Klan robes, but does admit to having darkened his face to dress up as Michael Jackson. He refuses to resign despite calls from Democratic colleagues to do so. Northram's deputy, meanwhile, Virginia attorney general Mark Herring, also acknowledged wearing "brown make-up" when he dressed as rap pioneer Kurtis Blow at age 19, hurling the state into a full-blown political crisis.

Public outcry has been fierce. But a recent survey on attitudes toward the practice paints a less flattering picture. A poll of Virginians is split evenly — 47 percent to 47 percent — among those who say Northram should resign and those who think he should remain in power.

Even more disconcertingly, a new Pew Research Center study found that 34 percent of Americans consider the darkening of skin to resemble a different race as part of a Halloween costume to be "sometimes acceptable." That all-in-good-fun take on blackface was the same one espoused by Megyn Kelly last October on her NBC morning talk show — a talking point she later recanted and apologized for, but not before the ensuing uproar led the network to buy her out of her $69 million contract.

Contrary to public opinion polls, however, no form of blackface has ever been OK. "There were always people who said it was racist, always commentaries about how horrible and demeaning it was," notes Yuval Taylor, co-author of Darkest America: Black Minstrelsy From Slavery to Hip-Hop. (After watching a blackface act in 1848, abolitionist Fredrick Douglass called the white performers "the filthy scum of white society" in a newspaper op-ed.) That a medical school student like Northram would engage in the practice in 1984 "seems so late for a white person to put on blackface," Taylor says. "By then, most people knew it was absolutely forbidden."

"A lot of people simply don’t know what racism is," notes Dr. Todd Boyd, professor of critical studies at USC School of Cinematic Arts. "They think it’s a cartoon version of racism where there’s an ugly evil person sitting in a corner who says they hate someone for the color of their skin. But it's systemic and institutional."

In fact, blackface is the oldest American show-business institution. It has its origins in minstrel shows, which began in New York City in the 1830s and quickly gained popularity among white audiences across the country. Performers were usually white men who would "black up" their skin using coal or dark shoe polish. Their mouths were drawn clownishly large, they donned woolly wigs and their performances depicted African-Americans as lazy, hypersexual and superstitious jokers.

But they typically had the last laugh. Soon African-American performers were donning blackface and embodying those harmful stereotypes themselves in black minstrel shows. (Bert Williams was one such performer — and his wildly successful act as the only black member of Ziegfeld Follies made him the highest-paid African-American star in the world in the early 1900s.) Says Taylor, "They experienced a kind of freedom onstage — and African-American audiences reacted to them favorably. It offered a means of escape."

Minstrel shows eventually gave way to the rise of Vaudeville, but blackface remained a staple of that variety-show circuit. With the rise of the movie industry in the 1910s, Hollywood was quick to cash in on blackface. D.W. Griffith's The Birth of a Nation, a 1915 silent epic that glorified the Ku Klux Klan, featured mostly white actors in blackface depicting black men as sexual predators and simpletons. The film drew protests from African-Americans, but went on to great box office success.

"Hollywood has always been very conservative about race," says Taylor. "So African-American actors immediately are put in roles codified by the minstrel shows. The plantation slave too lazy to do work — that becomes Stepin Fetchit. The Mammie figure is very characteristic, so it becomes Hattie McDaniel in Gone With the Wind." In blackface, white performers felt emboldened to perform in a broad and overly emotive minstrel style: Think Al Jolson on one knee, hand on his heart, singing about his "mammie."

"For Jewish entertainers like Jolson, blackface was a way of becoming white," says Nic Sammond, author of Birth of an Industry: Blackface Minstrelsy and the Rise of American Animation. "It forged an allegiance with the white Protestant majority." Jolson, known as "the king of blackface," justified the practice by positioning himself as an ally of the black community. Notes Sammon: "He understood blackness and minstrelsy as interchangeable."

(For example: Jolson campaigned to have Warner Bros. produce an all-blackface version of The Green Pastures, a 1936 movie depicting Bible stories told through the eyes of African-American characters. The studio shot that idea down, and the pic remains one of only six features films from Hollywood's golden studio era to feature an all-African American cast.)

Animation, too, provided a fertile Hollywood breeding ground for blackface and racist stereotyping. Even a character as universally adored and seemingly innocuous as Mickey Mouse can trace his DNA back to the racist practice, argues Sammond: "If you look at the way his face is made up — large painted mouth, painted eyes, white gloves, doing song-and-dance numbers, the plasticity of his body — that's all straight out of minstrelsy."

Disney has flatly denied these claims. But there's no denying that Dorothy from Kansas herself — Judy Garland, in a movie that came out just one year before The Wizard of Oz — donned blackface for 1938's Babes in Arms. And Fred Astaire went full blackface in 1936's Swing Time. The Hollywood Reporter took no issue with the latter performance, noting in its review that "Astaire in his tap solo in blackface equals his best work as a dancer who uses imagination as well as his feet."

Blackface finally began falling out of favor in the 1930s, but still found its way onto screens well into the 1950s. Sometimes it was justified as being part of a "historical" picture, such as 1943's Dixie. (The movie literally whitewashes history, suggesting that minstrel shows were born accidentally after a white actor with a black eye "covered his disfigurement in burnt cork," according to the THR review.) And Eddie Cantor, a Vaudevillian turned movie star affectionately known as the "Apostle of Pep," was doing blackface routines as late as 1948's If You Knew Susie.

But even as it vanished from screens, it never completely went away. "It went behind closed doors," says Sammond. "You begin to see it popping up inside localized charities, in frat houses, in Elks Lodges in the 1970s and '80s."

Modern Hollywood has occasionally dabbled in it since, finding convoluted and satirical ways to justify its existence. "You can always bring blackface back in some ironic way," notes Ed Guerrero, professor of cinema studies at New York University. There was Robert Downey Jr. in 2008's Tropic Thunder, who played a buffoonish white actor who insisted on donning blackface. Then there was 1986's Soul Man, starring C. Thomas Howell as a Harvard freshman who darkens his skin to qualify for a scholarship. "I would say Soul Man was a white-liberal attempt at affiliation and support of blackness," notes Sammond. "But it's still painfully naive."

White actors are not the only ones who do it, notes Guerrero. Besides the Chappelle sketch, Eddie Murphy has trafficked in African-American stereotypes for laughs. "His Buckwheat impersonation on Saturday Night Live? Black blackface is what that is," Guerrero says. Boyd points out that "the imagery and history of blackface is integral to black history though comedy."

"It’s hard in some ways to separate that from these cultural issues," notes Guerrero, who attributes its stubborn allure to "a power relation. Look at the governor's yearbook photo: A KKK figure next to a Sambo figure? That's a power relation." Adds Sammond, "Many whites in North America have a deep fascination with blackness and a deep desire to occupy what's good about being black without any of the repercussions."

Not surprisingly, the most pointed and astute take on blackface of the past 50 years has arguably come from Spike Lee, whose Oscar-nominated BlacKkKlansman depicts KKK members delighting to Birth of a Nation, and whose 2000 satire Bamboozled is centered around a TV network that re-popularizes blackface for a new generation. Bamboozled ends with a found-footage montage consisting entirely of demeaning representations of African-Americans — all of them produced by Hollywood in the first half of the 20th century.

Says Guerrero, "It really shows the catalog of white actors who have done blackface throughout the history of Hollywood."